Ethyl Bromide → HCID 90312753, compound

HRID 1523861Notes

Reaction equation

HRID 1523861 reaction equation
[C:1](=O)([S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[C:15]([F:17])[C:14]([C:18]2[CH:23]=[N:22][C:21]([NH2:24])=[CH:20][N:19]=2)=[CH:13][CH:12]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:45]([O-])([O-:47])=[O:46].[K+].[K+].BrCC>CO>[CH:45]([OH:47])=[O:46].[CH2:1]([S:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:12]=[CH:13][C:14]([C:18]2[N:19]=[CH:20][C:21]([NH2:24])=[N:22][CH:23]=2)=[C:15]([F:17])[CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 131733122HCID 131733122, compound

Product 1

HCID 90312753HCID 90312753, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of S-(4′-(5-aminopyrazin-2-yl)-5′-fluorobiphenyl-2-yl)methyl ethanethioate (100 mg, 0.28 mmol) in CH3OH (30 mL) were added Ph3P (147 mg, 0.56 mmol) and K2CO3 (78 mg, 0.56 mmol) followed by drop-wise addition of bromoethane (60 mg, 0.56 mmol). After 16 hours, the mixture was concentrated to dryness and the residue was purified by prep-TLC and followed by HPLC to give the title compound (70 mg HCOOH salt, 73%). MS (ESI): mass calcd. for C19H18FN3S, 339.12; m/z found, 340.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.38 (m, 1H), 8.07 (d, J=1.5, 1H), 7.89 (m, 1H), 7.48-7.40 (m, 1H), 7.37-7.21 (m, 5H), 3.71 (s, 2H), 2.42 (q, J=7.4, 2H), 1.13 (t, J=7.4, 3H).

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. customthe residue was purified by prep-TLC and

Sources & evidence

ORD record
ord-859f8a23633e4fd1a72b9f7e1bec83c8
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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